Synthesize acyl chloride from aldehyde

Question

I know it is usually easier to go from an acyl chloride to an aldehyde,

but is there a way to synthesize acyl chlorides from an aldehyde?

Edit:

Upon some textbook reading (Wiley: Organic Chemistry 11th Ed, Solomons), I realized that aldehydes could also be oxidized to carboxylic acids with chromic acid in aqueous acetone (the Jones Oxidation) and then you could react the carboxylic acid with thionyl chloride or phosphorus trichloride to yield the acyl chloride.

Another method was to convert the aldehyde into a cyanohydrin and through hydrolysis the -CN group could be then converted into $\ce{RCOOH}$. Then react $\ce{RCOOH}$ with $\ce{SOCl2}$ to get the acyl chloride.

Answer 1

There are many ways to affect the transformation, as you have realised, and many of which Loong has detailed below in his post.

This answer gives one method which I would be confident of working practically, in the lab, using common reagents. A full search of Reaxys of SciFinder would reveal conditions/methods more suitable for a specific aldehyde.

A Pinnick oxidation will convert an aldehyde into its corresponding carboxylic acid, which may then be treated with a reagent such as oxalyl chloride to give the desired acyl chloride.

Answer 2

In some cases, the direct reaction with chlorine is possible:

Clarke, H. T.; Taylor, E. R. o-Chlorobenzoyl chloride. Org. Synth. 1929, Vol. 9, 34; 1941, Coll. Vol. 1, 155.

 

In other reactions, radical chlorinating agents are used:

Ginsburg, D. The Action of t-Butyl Hypochlorite on Organic Compounds. II. Aromatic Aldehydes. J. Am. Chem. Soc. 1951, 73 (2), 702–704.

 

Hebbelynck, M. F.; Martin, R. H. Bull. Soc. Chim. Belg. 1951, 60, 54.

 

Arai, M. Bull. Chem. Soc. Jpn. 1962, 35, 1272; 1964, 37, 1280; 1965, 38, 252.

 

Winstein, S.; Seubold, F. H. Jr. Free radical reactions of aldehydes. J. Am. Chem. Soc. 1947, 69 (11), 2916–2917.